US4478741A - 4-Alkylcyclohexyl 4-alkanoyloxybenzoate and liquid crystal composition thereof - Google Patents

4-Alkylcyclohexyl 4-alkanoyloxybenzoate and liquid crystal composition thereof Download PDF

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US4478741A
US4478741A US06/489,890 US48989083A US4478741A US 4478741 A US4478741 A US 4478741A US 48989083 A US48989083 A US 48989083A US 4478741 A US4478741 A US 4478741A
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liquid crystal
compound
crystal composition
formula
trans
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Kenichi Nakagawa
Shigehiro Minezaki
Fumiaki Funada
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Sharp Corp
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Sharp Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups

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  • This invention relates to new nematic liquid crystal compounds and compositions containing said compounds for use in display devices.
  • liquid crystals Compounds which has a mesomorphic state or more between the solid and liquid state are called liquid crystals.
  • Liquid crystal compounds are known to exhibit fluidity at a certain temperature range, but to have an optically anisotropic property similar to that found in a crystal.
  • Various electrooptic effects exhibited by the nematic liquid crystal have been used in passive display devices such as in table-top and hand-held electronic calculators and wrist watches because of the low electric power consumption.
  • liquid crystal compound of the formula: ##STR2## wherein R and R' are straight chain alkyl groups each having 1 to 7 carbon atoms.
  • FIG. 1 shows an infrared absorption (IR) spectrum of trans-4-propylcyclohexyl 4-pentanoyloxybenzoate
  • FIG. 2 shows a nuclear magnetic resonance (NMR) spectrum of the compound
  • FIG. 3 shows an IR spectrum of trans-4-pentylcyclohexyl 4-pentanoyloxybenzoate
  • FIG. 4 shows an NMR spectrum of the compound.
  • a group of liquid crystal compounds according to the present invention have the following general formula: ##STR3## wherein R and R' are straight chain groups each having 1 to 7 carbon atoms. As is obvious from the formula, they have two ester linkages.
  • the compounds of the present invention can be produced, first, by condensing 4-hydroxybenzoic acid with straight chained alkanoyl chloride in the presence of hydrogen chloride scavenger such as pyridine, then reacting the resultant 4-alkanoyloxybenzoic acid with thionyl chloride or with phosphorous oxychloride to produce the corresponding acid chloride, and, finally, by condensing the acid chloride with trans-4-alkylcyclohexanol in the presence of a hydrogen chloride scavenger such as pyridine.
  • hydrogen chloride scavenger such as pyridine
  • the final product is purified by repeating the recrystallization.
  • the final product has the following chemical formula: ##STR7## wherein both --C 5 H 11 and --C 3 H 7 are straight chain alkyl groups. 2.6 g the abovementioned compound was obtained, and the yield based upon the amount of the compound was 76%. Crystals thus obtained of the compound was purified by recrystallization from aqueous 90% methanol three times.
  • FIG. 1 and FIG. 2 show an IR spectrum and an NMR spectrum of the compound obtained above, respectively.
  • trans-4-pentylcyclohexanol in the third step instead of trans-4-propylcyclohexanol
  • a final product trans-4-pentylcyclohexyl 4-hexanoyloxybenzoate of the following formula was obtained: ##STR8## wherein --C 5 H 11 is a straight chain group. It was recrystallized three times using 90% methanol.
  • FIG. 3 and FIG. 4 show an IR spectrum and an NMR spectrum of the compound obtained above, respectively.
  • the new liquid crystal compounds according to this invention have negative dielectric anisotropy, and can be used as a component of the liquid crystal compositions in which the dielectric anisotropy is made positive as a whole.
  • Such compositions can be used as a material for liquid crystal displays of, for example, the twisted nematic mode, the guest-host mode, and the cholesteric-nematic phase transition mode.
  • new liquid crystal compositions where the dielectric anisotropy is made negative as a whole can be used in liquid crystal displays of such as the DSM mode, the DAP mode and the guest-host mode.
  • the liquid crystal composition which contains above-mentioned new compounds will now be described. It consists of 55 wt % the cyanophenylcyclohexane liquid crystal, 13 wt % 4-fluorophenyl trans-4-heptylcyclohexanecarboxylate, 12 wt % 4-fluorophenyl trans-4-pentylcyclohexanecarboxylate, 10 wt % trans-4-cyclohexyl 4-hexanoyloxybenzoate, and 10 wt % trans-4-pentylcyclohexyl 4-hexanoyloxybenzoate.
  • This composition has been found exhibiting a nematic phase between -20° C. and 62.5° C.
  • the threshold voltage and the saturation voltage was 2.3 and 3.3 V, respectively, at 25° C. and with driving frequency 1 kHz.
  • the viewing angle dependence ⁇ (defined as a ratio of the voltage at which the transparency becomes 50% in case of the viewing angle of 15° relative to that at which the transparency becomes 90% in case of the viewing angle of 45°) of this cell was 1.32.
  • the liquid crystal composition according to the present invention has better characteristics for a display device in that the contrast will not substantially change with a change in viewing angle. To put it in another way, the duty cycle decreases to 1/14, much smaller than 1/10 of the prior art cell referred above. Therefore, the 40% increased multiplex driving can be available as compared with that of the prior art cell.
  • this invention makes it possible to produce the liquid crystal composition which exhibits a liquid crystal phase in a wide temperature range and has a low duty cycle. If the liquid crystal composition according to this invention is used in a display cell for use in, for example, clocks and table-top electronic calculators, complex display of various kinds of characters and patterns can be realized.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US06/489,890 1982-04-30 1983-04-29 4-Alkylcyclohexyl 4-alkanoyloxybenzoate and liquid crystal composition thereof Expired - Lifetime US4478741A (en)

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JP57074426A JPS58191781A (ja) 1982-04-30 1982-04-30 液晶組成物
JP57-74426 1982-04-30

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US (1) US4478741A (enrdf_load_stackoverflow)
JP (1) JPS58191781A (enrdf_load_stackoverflow)
DE (1) DE3315470C2 (enrdf_load_stackoverflow)
GB (1) GB2122606B (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4778621A (en) * 1985-10-14 1988-10-18 Chisso Corporation Ester compound
US4838657A (en) * 1984-11-15 1989-06-13 Seiko Epson Corporation Liquid crystal shutter

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3770654A (en) * 1970-05-02 1973-11-06 Seiko Instr & Electronics Nematic liquid crystal
DD105701A1 (enrdf_load_stackoverflow) * 1973-07-02 1974-05-05
US3876286A (en) * 1972-06-14 1975-04-08 Werk Fernsehelektronik Veb Use of nematic liquid crystalline substances
US4001137A (en) * 1971-08-07 1977-01-04 Merck Patent Gesellschaft Mit Beschrankter Haftung Nematic compounds and mixtures
JPS5557539A (en) * 1978-10-25 1980-04-28 Chisso Corp Cyclohexanol derivative
US4229315A (en) * 1978-01-07 1980-10-21 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystalline cyclohexane derivatives
DD146041A1 (de) * 1979-09-24 1981-01-21 Deutscher Hans Joachim Verfahren zur herstellung von kristallin-fluessigen 4-eckige klammer auf trans-4-n-alkylcyclohexanoyloxy eckige klammer zu-trans-n-alkylcyclohexanen bzw.4-eckige klammer auf trans-4-n-alkylcyclohexanoyloxy eckige klammer zu-3-subst.-benzoyloxy- eckige klammer auf trans-4-n-alkylcyclohexanen eckige klammer zu
DE3029378A1 (de) * 1979-08-03 1981-02-12 Chisso Corp P-cyanobenzoesaeure-trans-4-substituierte cyclohexylester
US4293434A (en) * 1978-08-08 1981-10-06 VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik Liquid crystal compounds
JPS5748945A (en) * 1980-09-09 1982-03-20 Dainippon Ink & Chem Inc Novel nematic liquid crystal compound
JPS5767538A (en) * 1980-10-14 1982-04-24 Asahi Glass Co Ltd Liquid crystal compund and liquid crystal display element containing the same
US4349452A (en) * 1979-07-18 1982-09-14 Merck Patent Gmbh Cyclohexylcyclohexanoates
US4419263A (en) * 1981-01-07 1983-12-06 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystalline cyclohexylcarbonitrile derivatives

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3770654A (en) * 1970-05-02 1973-11-06 Seiko Instr & Electronics Nematic liquid crystal
US4001137A (en) * 1971-08-07 1977-01-04 Merck Patent Gesellschaft Mit Beschrankter Haftung Nematic compounds and mixtures
US3876286A (en) * 1972-06-14 1975-04-08 Werk Fernsehelektronik Veb Use of nematic liquid crystalline substances
DD105701A1 (enrdf_load_stackoverflow) * 1973-07-02 1974-05-05
US4229315A (en) * 1978-01-07 1980-10-21 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystalline cyclohexane derivatives
US4293434A (en) * 1978-08-08 1981-10-06 VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik Liquid crystal compounds
JPS5557539A (en) * 1978-10-25 1980-04-28 Chisso Corp Cyclohexanol derivative
US4349452A (en) * 1979-07-18 1982-09-14 Merck Patent Gmbh Cyclohexylcyclohexanoates
DE3029378A1 (de) * 1979-08-03 1981-02-12 Chisso Corp P-cyanobenzoesaeure-trans-4-substituierte cyclohexylester
DD146041A1 (de) * 1979-09-24 1981-01-21 Deutscher Hans Joachim Verfahren zur herstellung von kristallin-fluessigen 4-eckige klammer auf trans-4-n-alkylcyclohexanoyloxy eckige klammer zu-trans-n-alkylcyclohexanen bzw.4-eckige klammer auf trans-4-n-alkylcyclohexanoyloxy eckige klammer zu-3-subst.-benzoyloxy- eckige klammer auf trans-4-n-alkylcyclohexanen eckige klammer zu
JPS5748945A (en) * 1980-09-09 1982-03-20 Dainippon Ink & Chem Inc Novel nematic liquid crystal compound
JPS5767538A (en) * 1980-10-14 1982-04-24 Asahi Glass Co Ltd Liquid crystal compund and liquid crystal display element containing the same
US4419263A (en) * 1981-01-07 1983-12-06 Merck Patent Gesellschaft Mit Beschrankter Haftung Liquid crystalline cyclohexylcarbonitrile derivatives

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
C.A., vol. 89, 129197m, (1978). *
Demus, D. et al., Mol. Cryst. Liq. Cryst., vol. 63, pp. 129 144, (1981). *
Demus, D. et al., Mol. Cryst. Liq. Cryst., vol. 63, pp. 129-144, (1981).
Demus, D., "Nonemissive Electrooptic Displays, pp. 83-119, (1975).
Demus, D., Nonemissive Electrooptic Displays, pp. 83 119, (1975). *
Gray, G. W., Mol. Cryst. Liq. Cryst., vol. 63, pp. 3 18, (1981). *
Gray, G. W., Mol. Cryst. Liq. Cryst., vol. 63, pp. 3-18, (1981).

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4838657A (en) * 1984-11-15 1989-06-13 Seiko Epson Corporation Liquid crystal shutter
US4778621A (en) * 1985-10-14 1988-10-18 Chisso Corporation Ester compound

Also Published As

Publication number Publication date
GB8311635D0 (en) 1983-06-02
GB2122606A (en) 1984-01-18
DE3315470A1 (de) 1983-11-03
JPS58191781A (ja) 1983-11-09
JPS6152193B2 (enrdf_load_stackoverflow) 1986-11-12
GB2122606B (en) 1986-02-05
DE3315470C2 (de) 1984-09-13

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